Al Capone

Alphonse Gabriel "Al" Capone (17 January 1899-25 January 1947) was the boss of the Chicago Outfit from 1925 to 1932, succeeding Johnny Torrio and preceding Frank Nitti. Capone was one of the most feared mobsters of all time, as he controlled the liquor trade in Chicago during Prohibition as a result of his political connections, his fierce temper, and his open warfare against the North Side Gang during the 1920s and 1930s.

Early life and valet career
Alphonse Gabriel Capone was born on 17 January 1899 in Brooklyn, New York City, the son of two immigrants from Salerno in southern Italy. Capone was expelled from Catholic school at the age of 14 for hitting a female teacher in the face, and he began working at a candy store and at a bowling alley. Capone met Johnny Torrio around this time, and Capone was recruited into Torrio's gang by Frankie Yale. Capone was slashed across the face with a knife by Frank Galluccio after Capone unintentionally insulted his wife, leaving Capone with notable scars on the left side of his face; he was nicknamed "Scarface". Capone claimed that he had served with the "Lost Battalion" in France during World War I and had injured his face during melee fighting with a German soldier. Capone left for Chicago, Illinois in 1919 to become a bouncer at one of James Colosimo's brothels, moving into the city alongside Torrio, Yale, and other gangsters who had been imported into Chicago by Colosimo.

Partnership with Darmody
In January 1920, Capone accompanied Torrio and Colosimo to Atlantic City, New Jersey, where they met with New York City criminals Arnold Rothstein and Lucky Luciano and Atlantic City political boss Enoch Thompson to discuss importing alcohol through the port city. Capone waited outside with Torrio's car, and he befriended Thompson's driver Jimmy Darmody. The two of them decided to make some quick money by ambushing one of Rothstein's liquor shipments as it left the city, and they hired Billy Winslow to assist them. On 7 January 1920, Rothstein's convoy found Billy Winslow's car overturned on the road and saw Winslow playing dead, halting their convoy. Capone and Darmody proceeded to hold up the five men, and Capone began shooting at them when he was startled by deer running through the woods. After massacring Rothstein's men, Capone and Darmody stole the liquor, with both of them taking cuts of the action; Capone took the liquor back to Chicago for resale. In May 1920, Torrio had Colosimo murdered due to Colosimo's refusal to enter the bootlegging business at the start of Prohibition, and Capone became Torrio's right-hand man.

Darmody was forced to flee to Chicago after Arnold Rothstein and Enoch Thompson went to war, as he was a wanted man in the eyes of Rothstein and Luciano. Darmody met up with his friend Capone at The Four Deuces, a brothel frequented by Torrio and other Chicago Outfit, and Capone scared Darmody one night by shooting a pistol at Darmody's pillow while he was sleeping, scaring him awake. Darmody criticized Capone for this joke, as the bullet grazed his ear and temporarily deafened him. Capone would quit his practical jokes in early 1921 after giving Torrio an exploding cigarette as a prank; Torrio told him to end his childish behavior.

Capone and Darmody both became buttonmen for Torrio, and the two of them took part in the extortion of businesses on the North Side of Chicago, including Irish Mob boss Charlie Sheridan's businesses in Greektown. This led to war between Sheridan and Torrio, and Capone and Darmody succeeded in murdering Sheridan and several of his men in a shootout at Sheridan's hotel. Capone would make a name for himself, and Torrio decided that he could be given more responsibilities due to his success. In November 1920, Capone and Torrio headed out to New Jersey to broker a peace deal between Rothstein and Luciano's organization and Thompson's organization; Darmody and his friend Richard Harrow had left Chicago to rejoin Thompson in Atlantic City for his fight against the D'Alessio brothers. Torrio's efforts succeeded, and Rothstein and Luciano agreed to pay Thompson $1,000,000 in cash and give up the locations of the last four D'Alessio brothers, and Capone would take part in the hit on Sixtus D'Alessio, shooting him in the head as he returned to his waterfront home with groceries.

Leadership of the Outfit
Capone would play a key role in the Chicago Outfit's gang wars in Chicago during the mid- to late-1920s, and he took part in the murder of Dean O'Banion in 1924. In January 1925, both Capone and Torrio were injured by North Side Gang gunmen in two separate incidents, and Torrio decided to retire to Europe and let Capone take over the organization. Capone killed 100 people when he bombed businesses that refused to buy liquor from him, and he became known as a cruel and fierce gangster. In 1926, he had O'Banion's successor Hymie Weiss murdered, and he had seven North Side Gang members massacred in the St. Valentine's Day Massacre of 14 February 1929 by gangsters dressed as policemen. Capone would repeatedly be arrested and released without charge, but he was finally nailed on income tax evasion in 1930. In May 1932, he was sent to Atlanta US Penitentiary, and he was moved to Alcatraz prison when it was alleged that he was receiving special treatment in prison. Capone was very ill, and he was wounded by another inmate in prison. In 1939, he was released on parole, and he became mentally ill; in 1946, he was said to have had the mental capacity of a 12-year-old child. Capone died on 25 January 1947 at his home in Palm Beach, Florida of cardiac arrest at the age of 48.